


Obey Me! Headcanons and Drabbles (Requests Open)

by humblepirate



Category: Shall We Date?: Obey Me!
Genre: Angst, Bigotry, Blow Jobs, Christian bigotry, Drabbles, Eventual Smut, Fluff, Hurt/Comfort, Oral Sex, Religious Guilt, Rough Sex, Self-Harm, Trans Character, Transphobia, headcanons
Language: English
Status: In-Progress
Published: 2021-02-16
Updated: 2021-03-14
Packaged: 2021-03-18 23:20:23
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 15,629
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29497932
Author URL: https://archiveofourown.org/users/humblepirate/pseuds/humblepirate
Summary: Exactly what the title says! I have a bunch of ideas not yet written, but I am definitely open to requests. Just leave a comment or message me on Tumblr at humblepirate!All explicit chapters are marked with an asterisk * after the title.
Relationships: Asmodeus (Shall We Date?: Obey Me!)/Reader, Beelzebub (Shall We Date?: Obey Me!)/Reader, Belphegor (Shall We Date?: Obey Me!)/Reader, Leviathan (Shall We Date?: Obey Me!)/Reader, Lucifer (Shall We Date?: Obey Me!)/Reader, Mammon (Shall We Date?: Obey Me!)/Reader, Satan (Shall We Date?: Obey Me!)/Reader, Simeon (Shall We Date?: Obey Me!)/Reader, Solomon (Shall We Date?: Obey Me!)/Reader
Comments: 5
Kudos: 32





	1. Trans!MC coming out headcanons

**Summary for the Chapter:**

> Prompt: The characters finding out that MC is trans and how they would react.  
> Characters: Demon brothers and exchange students  
> Rating: Romantic/Platonic (can be read either way)  
> Content: mentions of violent transphobia, self harm, accidental misgendering, gender dysphoria, parental abuse, conversion camps, minor spoilers for Lesson 16

**Notes for the Chapter:**

> I didn’t really specify what stage MC is at in their transition; I tried to leave it generic, though I think I came at it mostly from the perspective of someone who knows they're trans but hasn't told anyone or started externally transitioning because that's me lol. Please let me know if you have any questions or feedback!

Lucifer

  * He already knows since he saw MC’s file when he selected them for the exchange program. Of course, he had the good sense not to mention it to anyone besides Diavolo and Barbatos, who had also seen their file.
  * MC is at first terrified that Lucifer knows because he seems to know everything, but when he doesn’t bring it up and no one else says anything, they feel much more at ease.
  * The truth comes out (ba dum tssss) when MC and Lucifer are having a private conversation and MC is telling a story about their childhood.
  * “You remind me a lot of my mother, actually. She never yelled when she got angry, she was just very calm. Whenever she called me [Full deadname], even if she was smiling, I knew that meant I was in real trouble!”
  * Realizes they just accidentally outed themselves and starts to panic.
  * Lucifer isn’t sure if it would be better or worse to tell them he already knew, but ultimately decides that honesty would be the best call. 
  * It takes a few minutes for MC to understand, but when they’ve calmed down and realized that Lucifer has known they’re trans the whole time yet treated them with total support and didn’t tell anyone else, they’re so relieved.
  * If they didn’t already, trusts Lucifer now more than anyone else in the Devildom.
  * Eventually has a house meeting where they formally come out to all the brothers. Of course they’re all supportive, but it doesn’t hurt that Lucifer is standing behind MC the entire time and glaring at his brothers, silently promising that he will not hesitate to string them up if they ever purposefully misgender MC.
  * Bonus: after learning how shitty MC’s mother treated them, he makes a conscious effort to be less silent-scary around them and communicates more clearly when he’s angry.



Mammon

  * You know how in the first ep of _Ouran Highschool Host Club_ the light bulbs slowly turn on as the boys each realize Haruhi is a girl? Yeah, Mammon is Tamaki.
  * It’s not like anyone’s prying on purpose, but when you live with seven other people, it’s really hard to hide the fact that you’re trans. No one says anything, of course, waiting for MC to be ready to talk to them about it.
  * All of them except Mammon.
  * After he gets over the whole “ugh stupid human” phase, he becomes their closest friend in the house and they spend a lot of free time together. It gets to the point that he will just barge into their room whenever he pleases.
  * And of course, one day he stumbles in on them while they’re in the middle of changing.
  * Instantly they panic and scream at him to get out. He slams the door and runs to his room, confused and embarrassed and horrified that he invaded their privacy like that. 
  * Probably the first time in his entire existence that he’s felt truly ashamed.
  * After he’s had a few minutes to process everything, he goes to their room and slides an apology note under the door. He starts to walk away, assuming they’ll never want to talk to him again, but then they open the door and call out to him.
  * They tell him about the rejection and transphobia they faced in the human world and how they’d hoped this year could be a fresh start. He agrees not to tell anyone else until MC is ready to come out, though it kills him to stay silent whenever someone unknowingly misgenders them.
  * When MC finally comes out to the rest of the brothers, Mammon is the best hype man.
  * Co-president of the “Murder Anyone Who Misgenders MC” club.



Levi

  * Not quite as dense as Mammon, but it takes him a while to get there.
  * He starts to notice that whenever he plays games with MC, they always choose to play characters of a different gender than them. 
  * One day while they’re gaming, Levi casually mentions this, not even thinking what it could possibly mean. MC gets very quiet and excuses themself, saying they don’t feel very well.
  * Levi brushes it off at first, but when they don’t return his texts for the rest of the day and don’t come down for dinner, he starts to get worried. So he goes to the only person who might have the answers: his oldest brother.
  * Lucifer obviously doesn’t want to out MC without their consent, but Levi keeps pushing and pushing, so he encourages his younger brother to go to MC’s room and talk to them about it directly.
  * Levi doubts it’ll work but goes to their room anyway and knocks on the door. They don’t answer, so he takes out his D.D.D. and texts them.
  * LEVI: I’m sorry for what I said. I didn’t know it would hurt your feelings. Can we just pretend it never happened?
  * After a minute, they let him into their room and explain everything. Immediately Levi feels like a total moron for being so insensitive.
  * He supports them in the ways he knows: letting them choose their characters first when they game together, suggesting cosplays of characters with their true gender, and recommending openly trans musicians for them. 
  * It’s really hard to keep himself from using their correct name and pronouns in front of the others since they don’t want to come out fully yet, so he spends even more time in his room to avoid a mistake.
  * So relieved when they finally come out to the others.
  * Bonus: he feels a lot more comfortable cosplaying female characters with you because you don’t make him feel judged.



Satan

  * As smart and observant as he is, he doesn’t connect the dots right away. He also has way more important things to worry about than the gender status of the new human exchange student, so it’s far from his mind.
  * After they start to get closer, however, he starts to notice little clues about their behavior. They tend to wear a lot of baggy clothes that hide the shape of their torso and hips, and they get really uncomfortable whenever Asmo tries to talk them into a makeover. They also tend to stay in their room a lot and only shower late at night when the rest of the house is asleep.
  * So, Satan does what he always does when he’s unsure about something: he goes to the library.
  * He’s alarmed when his research tells him that MC’s behavior is indicative of someone who is deeply depressed and possibly harming themselves. Of course, how could he not see it? They had been unexpectedly yanked into the underworld and told they need to spend a year going to school with a ton of demons- anyone would be feeling a bit depressed after all that.
  * He immediately marches back home and right to MC’s bedroom. He knocks and they call out “Just a sec!” A few minutes later they open the door, wearing a large, bulky sweatshirt and hair a complete mess.
  * Satan, with his usual amount of tact, slams the door behind him and takes MC’s hands in his own.
  * “If you don’t want to be here, we understand. It must be a lot for you to handle,” he says. “But MC, I really wish you would come to me instead of hurting yourself.”
  * They are totally confused, until Satan explains his research. He’s scandalized when MC actually starts to _laugh_. Their safety is not a joke!
  * They sit Satan down on their bed and hesitantly explain that they’re trans. Suddenly, all the pieces snap into place.
  * Satan is ready to crawl under a rock for the next thousand years, but when he sees how vulnerable MC looks, he does his best to shake off his feelings and let them know that he supports them fully. 
  * Perfectly hides their secret until they’re ready to come out to the others.
  * “Protect MC” Squad is the one thing he and Lucifer are united on.



Asmo

  * Absolutely SMITTEN with MC from the moment he sees them.
  * They’re insanely shy at first, but he’s always loved a challenge.
  * In the first few days he teases them about their clothes and recommends some much more form-fitting outfits, but backs off when he sees how uncomfortable it makes them.
  * Unlike his brothers, Asmo is more than familiar with Gender Bullshit™ and starts to pick up on some of the signals they’re unwittingly giving off, though he has the tact not to say anything to them about it.
  * Once he stops being Aggressively Horny, he and MC actually start to become really close friends. He’s absolutely thrilled when they start to return his flirtatious teasing.
  * It’s not long before the sexual tension starts to ramp up between them. They spend more and more time together, usually lounging on Asmo’s bed and talking. Some part of them is always touching, their feet tangled together as they sit on the couch studying or their pinkies linked when they’re walking to class. 
  * Asmo is scared of ruining things, but he can’t deny his attraction to them. He wants things to get physical.
  * He starts with a kiss.
  * It’s chaste and quick, a good-night peck before he drops them off at their bedroom door, but they can’t get the feel of his lips out of their head for the rest of the night.
  * Gradually, their casual touches become more intimate and their gab sessions in Asmo’s room tend to turn into light makeouts more often than not. 
  * One night Asmo tries to reach under their shirt, but they quickly tug his hands away and start to remove his shirt instead. Their makeouts get steamier, but MC continuously rebuffs all of Asmo’s attempts to take their clothes off.
  * If he didn’t know any better, Asmo would think that MC wasn’t attracted to him. Since, of course, that is impossible, he thinks that perhaps he’s pushing them too fast and they’re not ready for a physical relationship.
  * It takes a herculean amount of will to summon them to his room and not immediately tackle them to the bed. 
  * He spills his insecurities to them, doing his best to hold back tears as he waits for their rejection. Instead, they start to _laugh_. He bared his soul, and now they’re just rubbing salt in the wound!
  * He’s readying a few choice insults when MC finally calms him down and explains that they’re trans. They’re self conscious of their body on a normal day, and even more so when it comes to physical intimacy. It doesn’t help that their partner is literally lust incarnate and they don’t want to disappoint him.
  * This time Asmo actually does start to cry, but only because he’s so happy that MC trusts him enough to reveal their true self to him.
  * Knowing this, Asmo is totally fine with taking things slow. It’s a few months before MC becomes accustomed to being sexually desired. Asmo doesn’t judge them or make them feel ashamed for their body, and the way he worships them, they start to feel more comfortable in their skin.
  * As MC’s confidence grows, they gather the courage to come out to the rest of the brothers. Asmo insists on sitting in their lap while they do it and gives his brothers a smile that says “If you ever hurt my baby, you’ll regret the day you were born.”



Beel

  * Also takes forever to realize it.
  * When MC arrives in the Devildom, they immediately bond over their love of macarons and spend many weekends trying out different recipes together.
  * During a holiday, Beel suggests the two of them bake a bunch of macarons and dye them pink and blue, then hand out all the pink ones to girls and the blue ones to boys. MC tries to hide their hesitation, but covers it with a smile and agrees.
  * Beel notices that they’re not as talkative as usual while baking. When the cookies are ready, he tries to hand them one of the wrong color. MC can’t hide their discomfort anymore and runs to their room.
  * Beel is completely baffled about why they had that reaction, so like he always does when he needs advice, he goes to Belphie.
  * Thankfully, Belphie is a lot more observant than his twin and points out that perhaps MC was made uncomfortable by the whole binary gender stereotypes thing. Beel honestly just saw it as an aesthetic and didn’t mean any harm by it, but once Belphie explains it to him he realizes why it would come off as insensitive.
  * After dinner he asks MC to talk privately and apologizes for his actions. When MC starts crying, he’s not sure what he did wrong but keeps apologizing and begs them to tell him how he can fix it.
  * When they calm down a bit, they explain that they started crying because they hadn’t expected Beel to be so kind. Even though he didn’t fully understand what was going on, he still apologized for hurting them, and that means a lot to MC.
  * They explain to him that they’re trans, what that means exactly, and how they were rejected by family and so-called “friends” when they first came out. 
  * They have to hold Beel back from going straight to the human world and obliterating everyone who hurt them.
  * After their conversation, Beel promises to keep their secret until they’re ready to tell the others. It hurts him too much to misgender or deadname them so he just avoids talking about them in third person altogether. He also does a lot of research on human gender and educates himself on how to be a proper ally.
  * When MC comes out to the rest of the house, Beel is right there holding their hand and encouraging them. The sweetest and most supportive teddy bear.
  * Bonus: he makes a batch of macarons to celebrate their coming out and dyes them in the colors of the trans pride flag.



Belphie

  * Honestly, he’s more concerned with getting out of the attic and destroying all humanity.
  * Once that whole ~debacle~ is wrapped up, however, and he starts really getting to know MC, they become closer. 
  * Their relationship is more intellectual and emotional than physical. Belphie tries making plans with them to hang out 1:1, but they always dodge his requests and will only spend time with him if someone else is in the room.
  * At first he figures that they’re just skittish around him after what he did, which is understandable. But he apologized and is trying to make up for it; why won’t they just forgive him??
  * He decides that they don’t actually care about him and are just pretending to be his friend. This makes him sulky and he stops talking to them. He ignores all their texts and leaves the room as soon as they enter it.
  * After a week of this silent treatment, Beel corners Belphie in their room and demands to know why he’s being so horrible to MC. Belphie is flippant at first- after all, they were the one who started blowing him off first- but his attitude changes when Beel says that MC came to him sobbing because they thought Belphie hated them.
  * Belphie finds MC in their room, though they don’t let him come inside and only talk to him over the threshold. He tells them to stop playing mind games and just tell him if they want to be his friend or not.
  * At that, MC breaks down crying and admits that they’re not upset with him anymore, but the ~incident~ triggered a memory of when their father did the same thing to them after they came out as trans. They love Belphie but being alone with him reminds them too much of that awful memory.
  * Of course Belphie feels rotten for how he treated them. He promises that he’ll never touch them _at all_ without their absolute consent and will do everything he can to make it up to them. He promises to keep their secret until they’re ready to come out to the others, and threatens to unleash literal Hell upon anyone who intentionally hurts them.
  * After they come out to the rest of the household, they start to feel much safer around Belphie and in general. 
  * He exhibits an unprecedented level of patience and understanding that no one in any realm has seen of him before. They drop their walls bit by bit, until one evening they wake up and realize they fell asleep leaning against his shoulder and didn’t have a single flashback or panic attack.



Simeon

  * He bonds with MC pretty quickly since they have a couple classes together. They feel comfortable going to him with questions about the Devildom and the demon brothers since he’s known them for so long, and he feels a bit protective of them as a non-magical human in a world of demons.
  * He doesn’t pry into their religious beliefs, though they give a few occasional hints that they may not have had the best relationship with the Christian church when they were in the human world.
  * One afternoon, they’re going for a walk together when MC asks out of nowhere, “Is it a sin to want to change your gender?”
  * Simeon hesitates. He knows that gender is a very complicated concept for humans and they have many different interpretations of God’s word. He has a feeling that MC is expecting him to say yes, and that breaks his heart a bit.
  * “Do you want the truth?” he asks. They nod eagerly. “The truth is that God loves all His children, and would never consider it a sin to live as one’s authentic self.” He gives them a gentle smile. “It’s not a sin to love yourself.”
  * They frown in confusion, clearly not expecting that answer. After a few minutes of walking in silence, they bid Simeon goodnight and hastily leave.
  * The next day, MC asks him to walk them home from class. As they walk, MC confesses that shortly before they were summoned to the Devildom, they came out as transgender and it went horribly. They lived in a small, Christian town and were shunned by their entire community. Everyone told them they were an abomination and would go straight to hell.
  * “Well,” Simeon says, “technically, they weren’t wrong.”
  * It takes a minute for MC to realize the joke, and then they start laughing until tears are streaming down their cheeks, and then they’re crying while Simeon holds them gently.
  * He knows that humans have long misinterpreted his Father’s word and it kills him that their ignorance brought MC so much pain. It takes more than a little willpower to stop himself from zooming up to the human world and exacting his righteous vengeance on all of them.
  * He dutifully keeps their secret until they’re ready to come out to the others. He’s very calm and casual and doesn’t make a huge deal about it, but anytime someone even accidentally misgenders them, he shuts that shit down in a heartbeat.
  * Bonus: he asks you and Solomon for all the dirt on the most bigoted sects of Christianity in the human world so he can ask God to send them a couple “messages.” Spoiler: Westboro Baptist headquarters are swallowed in a lava sinkhole.



Luke

  * Look, he may be hundreds of years old but he is still Baby and believes that humans are fallible but ultimately Good At Heart.
  * Oh boy, does that change quickly when he arrives in the Devildom.
  * The Celestial Realm is a bit behind in the education department, so when Luke attends history classes at R.A.D. and learns about all these awful things that humans have done in the name of God, he immediately declares it Devildom propaganda bullhockey.
  * He’s hanging out with MC after class one day and starts ranting about this, and suddenly MC interrupts him to say, “Actually, uh… the Crusades literally happened.”  
At first Luke thinks they’re pranking him, but between MC, Solomon, and some human world history textbooks borrowed from Satan, they convince Luke that, yes, humans have inflicted untold suffering upon each other because of religion.
  * Obviously he’s crushed and feels like his entire world view has kind of flipped around. He’s always seen the universe as good vs. bad, angel vs. devil, with angels appointed to protect innocent humans from the corruption of demons.
  * It makes him so sad to think that someone he loves might have been hurt by these humans’ ignorance. He turns to MC, desperate for reassurance, and says, “You haven’t experienced anything like that, have you?”
  * Hesitantly, MC admits that they have. After Luke pushes, they say that when they came out as transgender to their family, they were sent to a Christian conversion camp in order to “cure” them of their “perversion.”
  * Luke gapes at them. “BUT THAT’S NOT EVEN A SIN!”
  * MC starts laughing, and when Luke looks scandalized, they explain that they’d been terrified to come out to him because they assumed he was like the bigoted Christians from their hometown. They’re relieved to learn that God doesn’t give a hoot what gender you are as long as you’re happy.
  * It takes a while to explain to Luke the intricacies of human gender identity and why it’s such a big deal to them. Once they explain it, he will be their fiercest supporter and always hype them up when they’re feeling down.
  * When they get the courage to come out to everyone else, Luke is immediately in the demon brothers’ faces threatening them with something even worse than God’s own wrath if they ever hurt MC. He’ll warm up to them eventually.



Solomon

  * As the only other person from the human world, MC wants to come out to him pretty quickly because he’d be the best one to understand human concepts of gender. Still, they’ve learned to be cautious and don’t want to let their guard down around the shady sorcerer until they’re 200% sure he can be trusted.
  * Honestly, Solomon does not do a great job at convincing MC to trust him. With pacts with seventy-two demons, it’s hard to even tell what side he’s on. 
  * Over time, however, as they become closer and discover things they have in common, the trust between them slowly builds. Solomon even starts teaching them some basic magic, and they have a surprising knack for it.
  * When one of his spellbooks goes missing, he assumes Simeon or Luke borrowed it. He doesn’t expect to see MC curled up in a corner of the library and eagerly copying something from the book onto a piece of parchment.
  * He doesn’t confront them right away. Instead he waits until they step away to grab a drink of water, then he sidles over to their table and looks at the spell they’d been writing down.
  * He’s startled to see it’s a spell of gender transformation. When MC comes back and sees Solomon standing there, they’re mortified and quickly try to explain it away, but he’s surprisingly understanding.
  * They find a private study room in the library and MC explains how they came out once before and it went horribly. They were too nervous to tell Solomon and were going to attempt to cast the spell themselves, though it was unbelievably risky even for a seasoned magician.
  * Solomon was hesitant. He could try to cast the spell and it would be as if they had been that gender their entire life. No one would remember them as anything other than their true gender and name. It’s risky, but he would be willing to do it.
  * When he explained that, though, MC became very somber. They had a lot of complicated feelings about their past, and as painful as it was, the process of realizing their truth and coming out is just as important to them as living as their true self. 
  * After talking it over, MC decides to hold off on the spell and think about what they want to do next. Solomon is endlessly supportive and does all he can to protect their secret.
  * A few days later, they tell him they’re ready to come out to the others. He stands beside them when they announce it and makes sure everyone in the room sees his hand subtly hovering over his wand, just in case.
  * Bonus: MC keeps practicing their magic and experiments with temporary glamors to test out different body shapes before they commit to any permanent changes. It’s awesome to relieve a bit of dysphoria while they’re still figuring things out.



**Notes for the Chapter:**

> I didn't include Diavolo and Barbatos in this one because I honestly don't interact with them enough in the game to have a good feel for their personalities, but I might do them in future chapters if people want.
> 
> I hope you enjoyed this! It came to me in the middle of the day and I wrote it in a fevered rush during work. If you have any requests, feel free to drop them in the comments! Thanks for reading!!


	2. First Date with a Trans!MC

**Summary for the Chapter:**

> Prompt: Trans!MC’s first date with the boys  
> Characters: All dateables  
> Rating: Romantic/SFW  
> Content: mentions of transphobia and child abuse, implied suicidal thoughts, gambling, kissing, drinking alcohol (no drunk hanky panky though), a teeny bit NSFW for Lucifer and Mammon

**Notes for the Chapter:**

> This fic was requested by RebornMK and it was so fun to write!! Thank you for the amazing request friend. <3

Lucifer

  * He’s got two tickets to the Devildom Metropolitan Opera and invites you along.
  * You assumed at first that he had initially planned to go with Diavolo and are surprised when you find out that he purchased the tickets with you in mind.
  * You’ve never been to an opera, never mind one in actual Hell, so you enlist Asmo’s help in finding an appropriate formal outfit. When he finally deems you date-worthy, you step into the front hall and find Lucifer waiting for you.
  * It’s a perfect movie moment: he can’t keep his eyes off you as you descend the stairs, and you’re equally captivated by his immaculate suit. It’s made of a strange material blacker than any fabric you’ve ever seen, yet it glimmers in the light as if it’s covered in a billion tiny constellations. Paired with an elegant red tie and ruby cufflinks, he looks like he just stepped off the cover of _Handsome Devil Monthly_.
  * He takes your arm like a real gentleman and leads you outside to the limo he’d rented just for your date.
  * It’s honestly a bit overwhelming; you’ve never had a partner fawn over you this much, and you’re not sure how to react.
  * Lucifer picks up on your discomfort and keeps the conversation flowing easily on the way to the theater. He can put you at ease so effortlessly, and by the time the limo stops, you’re feeling much more comfortable.
  * As you join the other demons climbing the steps in their fanciest regalia, you catch a couple stares and fragments of whispers. At first you fear they’re judging you, but then you realized the attention is directed toward Lucifer.
  * Right. You’d forgotten that you’re on a date with one of the most powerful demons in the entire realm.
  * He definitely didn’t skimp on the tickets. You have your own private box at a perfect angle to see the entire stage. Some of the instruments you recognize, but most of them are strange conglomerations of horns and spikes that produce sounds you’ve never heard before.
  * You enjoy the performance, even though you don’t know any of the compositions. As the show winds down, the conductor stands up and announces that their final song was a special request from a highly revered guest, with a not-so-subtle glance at Lucifer.
  * Before you can ask Lucifer what he’s talking about, the orchestra begins a sweet, romantic piece that picks at the back of your brain. It takes you a minute to realize that it’s the duet you and Lucifer sang when you performed in the _TSL_ musical together.
  * You look over at him and see he’s watching you with a small, hopeful smile on his face.
  * All you really want to do in that moment is grab him and kiss him, but you remind yourself that he still has a reputation to keep up.
  * Waiting for the applause to end and the audience to file out of the theater is absolute torture. 
  * When you are finally alone with Lucifer in the limo, you throw your arms around him and kiss him with all the pent-up adoration inside you.
  * He reciprocates immediately, pulling you into his lap and biting your lip as he returns the kiss.
  * beyonce_partition.mp3
  * His hand moves to your zipper and you freeze up.
  * He quickly pulls back and apologizes, but you assure him he’s fine, you want it too… but there’s something he ought to know before you go any further.
  * He acts way too casual when you tell him that you’re trans, and he admits that he knows already because it was on your file when he chose you for the exchange program.
  * You’re not sure whether to be relieved or mortified. Thankfully, Lucifer, in a rare moment of vulnerability, assures you that he cares deeply for you- _all_ of you. He would do anything to make you comfortable and show you just how much he adores you.
  * You lean in to whisper something in his ear.
  * His face turns bright red and he quietly slips the limo driver an extra hundred grimm to take the long way home.



Mammon

  * He just finished reading _Sure Ways to Win at Poker_ and he needs a second to help him try out his new tricks, so naturally you’re his first choice.
  * You agree to go on the condition that he buys your drinks. He doesn’t have much of a choice, so he grudgingly accepts.
  * You make a joke that if he’s buying you drinks, it’s basically a date. You mostly said it to fluster him, but to your surprise he mumbles through his embarrassment, “Well, I wouldn’t… ya know… hate that idea.”
  * So it’s a date.
  * You have to arrive separately to make it look like you aren’t together. The casino is very high-scale and you dress in your nicest clothes to fit in. 
  * Even though you’re supposed to pretend you don’t know each other, he immediately spots you when you walk in and his jaw drops.
  * You saunter over to the table he’s at and take a seat next to him as the dealer is starting the next game. You pretend to think hard before placing your bet down. When you glance at Mammon, he’s trying hard not to appear like he’s staring at you. You subtly nod at the table to remind him the game is starting and he fumbles with his chips before sliding them into the pot.
  * The two of you had worked out an ingenious (in Mammon’s mind) strategy to cheat the game. He’d insisted it’s not really cheating because there’s two of you, which makes absolutely no sense, but as long as you get free drinks you’re not complaining.
  * He’s totally in his element here. Who knew Mammon was actually a really amazing actor? He plays it safe for a few rounds, purposefully making rookie errors to give his opponents a false sense of confidence. As the pot grows larger, he adjusts his strategy and his winnings slowly start to climb.
  * It’s honestly kind of hot seeing him so confident and smooth, you can’t help teasing him just a little bit.
  * You pretend to be focusing very hard on your next move, while under the table you casually rub your thigh against Mammon’s. His spine stiffens and his composure almost breaks entirely before he gets ahold of himself again.
  * You hold your cards in one hand while the other slides surreptitiously beneath the table and into his lap.
  * He chokes on his drink and another player thumps him on the back a few times to help him calm his breathing. He makes an excuse about accidentally swallowing the wrong way while glaring helplessly at you.
  * You’re getting a few odd looks from other patrons, so you decide to keep it safe and remove your hand. The pout Mammon gives you is simultaneously adorable and infuriating; if he isn’t careful, he’ll give away your con.
  * He waits until there’s a small mountain of chips in the pot before he finally executes his big move. He sweeps the table and everyone groans as he collects his enormous winnings.
  * You stay behind and pretend to share the others’ disappointment while Mammon cashes out. A few minutes later he texts you to meet him behind the casino and you manage to sneak away from the crowd.
  * As soon as you step into the alley behind the building, Mammon pulls you into a thrilling kiss that leaves you dizzy.
  * His bank account is now teeming with beautiful, beautiful grimm, and he couldn’t have done it without you! Despite your temporary… ahem, _distraction_ back there. Not that he really minded it.
  * You kiss him again and he pulls you close, his hand sneaking toward your waist as he mumbles about returning the favor. Suddenly, you feel cold all over and you jerk back.
  * Oh, no. He did it again, opened his stupid mouth and made you uncomfortable and now you’ll never want to be around him again-
  * You give him another quick kiss and tell him that it’s not his fault. You’re self-conscious about physical intimacy because of, well- some pretty awful trauma from your ex.
  * After you came out as trans, your ex had treated you horribly and the whole experience made you reluctant to trust anyone else. This is the first date you’ve been on since then and you don’t want to ruin it.
  * Mammon assures you that of course you didn’t ruin it, and he’s happy you trust him enough to tell him something so personal. He’s used to being dismissed as too stupid or impulsive to be trusted so this is really significant to him. He likes you a whole lot and would never want to make you uncomfortable or feel less than amazing.
  * You lean in to kiss him again, but a loud _crash_ interrupts you. The casino bartender comes rushing into the alley, followed by two bouncers, and starts yelling that Mammon forgot to pay his tab.
  * The two of you _nyoom_ right on out of there.
  * Bonus: “Technically, since you didn’t actually pay for my drinks, it didn’t count as a real date.” “You mean swindling innocent demons out of their hard-earned grimm isn’t romantic enough for you?”



Levi

  * The two of you have been dying to try out this new arcade that just opened downtown, so when you finally have a free weekend, you make a plan to visit together.
  * It’s basically a gamer’s wet dream. The room is filled with different types of games, from arcade cabinets and first-person shooters to VR and PC stations. Each game has a little tablet where you can order your food and drinks, which are delivered to you by servers cosplaying as famous video game characters.
  * Levi immediately drags you over to an old school two-person racing game. You match each other win for win, and when you finally let someone else have a turn the score is tied. You suggest a Rock Band battle to break the tie.
  * Turns out, he really is an agile gamer. No matter which instrument he plays, he decimates your score. He’s soon five wins ahead of you and still has plenty of grimm to burn, so you scout the arcade for something you’re better at.
  * Ah-ha! They have some off-brand Mortal Kombat tucked among the classic games. As soon as you start playing, muscle memory takes over and you quickly start racking up wins. You can tell Levi’s confidence is faltering as you catch up to him, and soon the two of you are tied once more.
  * You’re both getting pretty tired, but you need one more game to settle this competition for good. Then you spot it: a dancing game set up in the middle of the floor.
  * It’s perfect. Levi hates when other people watch him, and he’s such a shut-in that there’s no way he would beat you at a physical game.
  * You take your places on the light-up miniature dance floor. The music begins, and you’re off- following the character on the screen, adding a little shimmy to your moves to really ramp it up. Other gamers start to gather around to watch you.
  * You chance a quick look at Levi and realize that he’s keeping nearly perfect time with the game. Who knew he could even move his hips like that?! Your heart sinks as you understand you severely underestimated him.
  * The song speeds up as it goes into the chorus and you pour all your concentration into winning. Every so often you peek at Levi. He’s totally captivated by the game, ignorant of the sweat running down his temples or the exhaustion in his legs, focused entirely on winning.
  * When the song ends, you’re both panting hard and covered in sweat. The scores tally up on the screen and the numbers are nearly even- then Levi’s ticks up just a few more points.
  * The crowd around you starts cheering and giving him high-fives. He’s high on the adoration of the crowd and doesn’t notice as you slip away to let him enjoy himself while you order some waters.
  * When he extricates himself from his admirers, his face is bright red both from the workout and embarrassment. He’s not used to having so much attention from other people, but he admits it wasn’t _completely_ terrible.
  * You find a table in a rather secluded corner to sit and drink your waters. You each down three glasses before you feel recovered enough to talk. A waitress in a skimpy maid outfit brings you some appetizers, and as she’s walking away you catch Levi’s eyes following her.
  * When you ask if he’s interested in her, he quickly goes bright red again and starts sputtering about how he was just admiring her costume.
  * “Good, because it would be quite rude for you to ogle someone else while you’re on a date with me.”
  * Cue choking on his own saliva.
  * He wasn’t sure if you’d consider it a date and was fine with just quietly pining after you while you remain oblivious to his affections. Now that he has verbal confirmation that you return his feelings, though, he has the sudden urge to retreat into his room.
  * He shyly explains that he hasn’t dated anyone- well, basically ever. You assure him that you’ve only ever been in one relationship before and it ended poorly so it’s not like you’re a dating expert either.
  * When he asks what caused the breakup, you hesitate before telling him that your ex reacted really angrily when you came out as trans. Since then you’ve stayed away from any type of dating because you don’t want to repeat the experience.
  * Levi replies that anyone who would make you feel lesser because of who you are doesn’t deserve your time, and he adores every part of you.
  * Even though you’re surrounded by sweaty gamers, it feels like you’re on a little island away from everyone else. Knowing Levi supports you and loves you no matter what erases all the bad feelings from that past relationship.



Satan

  * It takes him about an hour of pacing in his room to get up the confidence to ask you out, but you’d never know from the way he strolls up to you and casually announces that you’re going with him to the new exhibit at the Museum of History.
  * You’re used to Satan phrasing requests in the form of commands, so thankfully for him it doesn’t phase you.
  * He insists on getting to the museum right when they open so you have plenty of time to explore the exhibit. You think that’s a bit dramatic, but when you arrive you understand what he meant.
  * The exhibit is on human world shipwrecks, and it’s _enormous_. There are original ships and even a couple replicas that you can go inside to explore. The museum is also offering a scavenger hunt quiz with a prize for anyone who can answer all the questions.
  * You and Satan have a blast exploring the exhibit. You never knew there were so many fascinating details about human world maritime history, and it’s especially fun reading about it from the perspective of Devildom historians. 
  * Satan really enjoys asking you about the human world elements he doesn’t know much about. You suspect that he’s pretending not to know so that he can hear you tell it. At first you think he’s making fun of you, but the way he smiles as he listens to you makes you think maybe he just likes to hear you speak.
  * By the time you finish the scavenger hunt, the museum is nearly ready to close. You’re glad now that Satan suggested arriving early (though it might not have taken so long if he hadn’t insisted on searching every single artifact and display in case there was a bit of information you might have missed).
  * The prize is a replica of a captain’s hat, right down to the ship name stitched into the brim. You offer it to Satan since he honestly did most of the work, but he plops it on your head, insisting it suits you better.
  * When you step outside, you realize how hungry you are after walking around the museum all day. Thankfully, you find a food truck nearby and sit down in a park to eat and rest your feet.
  * While you rest, the conversation pivots from the museum and history to more personal questions. It’s odd to you that a powerful demon would be so interested in your boring life, but it’s also quite flattering.
  * When he starts to ask more questions about your family, you try to hide your discomfort, but Satan being himself picks up on it immediately.
  * He has the sense not to pry, but after the day you’ve spent with him, you feel like you can trust him.
  * When you explain how your family reacted when you came out, he listens patiently and lets you get it all out. It’s a sad story, but alongside the sadness is an anger as well- anger at how you were robbed of the support you needed and the ignorance you faced from people who were supposed to love you unconditionally. He understands that far too well.
  * You’ve never told anyone else this story before and it is surprisingly cathartic. When you’re done, Satan puts his arm around you and lets you lean on his shoulder. He’s not the best at comforting people with words, but he makes damn sure you know that he’ll always protect you from being hurt like that again.



Asmo

Okay so Asmo's actually got SO long because he's Extra (TM) so I'm uploading his as a separate chapter!

Beel

  * You assumed that his ideal first date would be to go out for a meal or something, but he actually suggests a painting class!
  * It’s a perfect first date setting because you get to spend time together but don’t have to worry about keeping your partner entertained the whole time, and there’s less pressure since you’re surrounded by other people.
  * Today’s painting is a still life of a vase of autumn sunflowers. You both try your hardest, but the end results look more like a pile of colorful sticks. It doesn’t matter because you both had a ton of fun!
  * While you wait for your paintings to dry, you offer to treat Beel to some ice cream as thanks, and of course he accepts immediately.
  * He offers you a bite of his cone, which is a very sweet gesture, but you’re not sure that “vampire bat crunch” would agree with your stomach, so you stick with your plain vanilla with sprinkles.
  * You walk around downtown and chat while eating your ice cream. Outside of the house, when he’s not busy keeping the peace between his brothers or working on school assignments, Beel shows a much friendlier and more humorous side of himself.
  * When you go back to pick up your paintings, the instructor comments how you have a real eye for color. You get a bit flustered at the compliment, which Beel finds totally adorable.
  * As you’re heading back to the house, he brings up the compliment and says that you have a natural artist’s eye. You get flustered again and shyly mention that you really wanted to be a painter when you were younger, but your parents thought it wasn’t a proper career for a-
  * You stop as you realize you just revealed your assigned gender.
  * Beel walks a few more paces before he notices you’re no longer beside him, and turns to ask you what’s wrong.
  * It’s not that he wasn’t paying attention; he just didn’t want to say anything until he knew you were comfortable discussing it.
  * You timidly explain that you were assigned a particular gender at birth, but as you got older you realized that it wasn’t your true gender. He just nods along, completely understanding. The only part he doesn’t get is why your parents rejected you for something more or less arbitrary.
  * When you explain transphobia in the human world and that your family was not the most compassionate when you came out, he starts to transition into his demon form- something that only happens when he’s especially emotional.
  * It’s actually kind of scary to see him go from sweet and understanding to cold and angry so suddenly.
  * You’re quick to assure him that you’ve long since cut ties with your biological family and there’s no need for him to head up to the human world and slaughter them all.
  * Once he’s calmed down, he apologizes profusely for getting worked up but you honestly thought it was kind of hot.
  * To your embarrassment, he hangs the paintings above his bed, so he’ll always have something to remember the best first date he’s ever had.



Belphie

  * He absolutely did not see this coming. You want to go on a _date_ , with _him_ of all people (demons)? 
  * After he gets over the excitement of finding out his crush is reciprocated, he realizes that he’s never been on an actual date before. The only person he really ever hangs out with is Beel, and he has no idea what you’re supposed to do on a date. 
  * Thankfully, you already have a plan. Late at night, the two of you bring a ton of pillows and blankets to the observatory and make a little blanket fort in the middle of the room, making sure to leave the top of the fort open.
  * You turn off all the lights and lay down in your snuggly fort, and through the glass ceiling you can see the endless galaxy above the Devildom.
  * It’s very different from the sky you see in the human world. There are thousands more stars and they glow with a shimmering purple light. The planets and moons are very similar to the ones you know, but there are far more of them and they are big enough to see without a telescope.
  * Belphie points out the demon constellations and tells you the stories behind them. You suspect he’s making some of them up, but you don’t mind because his voice is so calming to listen to.
  * He asks you to describe some of your human world constellations, so you do. After a few minutes you can hear him gently snoring, snuggled up close to your side. It’s not long before you fall asleep as well.
  * When you wake up, you can’t feel Belphie’s warmth next to you. You open your eyes and see he’s scooted a few feet away and is awkwardly playing with his hands.
  * “Sorry,” he says, “I didn’t want to make you uncomfortable.”
  * You’re confused, until you glance down and realized your shirt rode up in your sleep so that your chest is completely exposed
  * You quickly yank it back over yourself and try to stammer out an excuse, but Belphie puts a calming hand on your knee.
  * “Do I look like someone who gives a shit about arbitrary human concepts like gender?” he scoffs.
  * You’re still totally embarrassed, so Belphie moves closer to you and explains that he only moved away because he didn’t want you to think he was taking advantage of you being half naked. He doesn’t care what’s under your clothes; he had a wonderful time last night and would absolutely like to nap with you again sometime.
  * His words reassure you and ask if he wants to go grab breakfast together. The other may tease you when they see the both of you leaving the observatory still wearing your clothes from yesterday, but they can laugh; you don’t really care what anyone thinks, because Belphie is there for you.



Solomon

  * Even though he’s also from the human world, he’s spent most of his life studying magic and never really immersed himself in human pop culture. Therefore, you make it your personal mission to get him up to speed.
  * After days of cajoling and teasing, you finally convince him to (begrudgingly) join you for an 80s movie marathon in your room.
  * He makes a great effort to act like he doesn’t care, but an hour in he slowly begins to drop the facade. By the end of the second movie, he’s visibly engaged, tearing up at the emotional parts and even laughing aloud a couple times.
  * He finally understands some of Asmo’s pop culture references.
  * It’s getting late when the last movie ends, but Solomon starts talking about how much he enjoyed it and asking you about your favorite parts. It occurs to you that he’s stalling because he doesn’t want the date to be over quite yet. 
  * Precious tsundere doesn’t want to admit he enjoys spending time with you.
  * He starts looking up the best 90s movies for your next date and suggests _Mrs. Doubtfire_.
  * panic.jpg
  * You tell him you don’t really like that movie, but he knows you well enough to tell there’s something else going on. After he pushes you, you finally tell him that you’re trans and your first coming out was really traumatizing. The transphobic elements of the movie just remind you of that time which you’d rather forget.
  * Instantly Solomon is ashamed of himself for not doing his research on the film before suggesting it, as well as pressuring you to reveal personal information when you clearly were uncomfortable with it.
  * You tell him that it’s okay, he couldn’t have known, but that’s not good enough for him. As soon as he gets home he starts researching uplifting films by trans creators so you can continue his pop culture education without endangering your own mental health.
  * Bonus: he also starts to research more glamour spells to help with your dysphoria.



Simeon

  * It’s been months since you were last in your own worlds, so he suggests you have lunch at a multicultural restaurant that serves angel and human food as well.
  * You have an amazing time trying each other’s food and talking about favorite meals from your home worlds. You don’t actually realize it’s a date until halfway through the meal, after he casually mentions that it’s one of the best first dates he’s ever been on.
  * Cue blush!!
  * Simeon actually thinks it’s totally adorable how flustered you get by his comment.
  * After lunch, you take a walk around downtown and admire the sights. You haven’t had many opportunities to explore the Devildom outside of R.A.D., and you’re both fascinated by the contrast of ancient architecture with modern shops.
  * Simeon has been so polite, keeping his hands to himself and giving you a respectful distance while you walk, that you start to wonder if he was kidding when he said it was a date.
  * Also lowkey ashamed because you have not been subtle about ogling the way that outfit shows off his hip bones.
  * You finally work up enough courage to take his hand in what you hope is a cute and romantic gesture.
  * His cheeks darken but he doesn’t say anything, just gives your hand a gentle squeeze. Mission = success.
  * You had planned to keep things chaste considering he’s, well, a literal angel… but damn, his shoulders. Also cannot overemphasize those hip bones. Sharp enough to cut glass, I tell ya.
  * When he suggests the two of you take a break from walking, you agree a little too eagerly to be innocent. You scout out an empty bench in a nearby park and sit close enough to him that your shoulders lightly brush against each other.
  * You continue to admire the sights and chat about nothing particularly important, while your consciousness is wholly focused on the sensation of his skin touching yours.
  * After a little bit, the conversation dies out and you sit in a comfortable quiet, just enjoying one another’s company.
  * Evening is creeping in and the temperature is dropping. You hadn’t planned on staying with him so long so you didn’t bring a sweater, but when Simeon notices you shivering, he wraps you in his cloak and holds you against his side.
  * He’s so warm and comfortable you could honestly stay like this forever. You just hope he doesn’t notice how quickly your heart is beating at the closeness…
  * Somewhere a clock chimes the hour, and you realize you’re going to be late for dinner if you don’t leave soon. You start to extract yourself from Simeon’s hold, but he stops you with a gentle hand on your arm and a whisper of your name.
  * When you turn to him, he’s blushing like a tomato and looks a bit like a nervous fawn. You’re terrified that maybe you did something to upset him, but his grip tightens just a fraction, the fear in his eyes abates-
  * He initiates the kiss, but you are the one to escalate it. After spending the afternoon admiring his body and thinking about how nice it would be to have it pressed against you, it’s a relief to finally know what he tastes like.
  * And goddamn, is he a good kisser.
  * But of course, because you can’t allow yourself to enjoy things, the guilt starts to creep in and you reluctantly break the kiss.
  * You just blurt it out. You tell him how coming out as trans made your dating life hell because you were terrified your partner would become violent if they knew. You don’t want him to think you were trying to trick him into dating you without sharing the full truth of your identity.
  * Of course Simeon would never feel like you were tricking him by protecting yourself, but he understands why you feel that way.
  * He assures you that there is absolutely nothing wrong with who you are and that he will support you in whatever way you need.
  * Also says that he will personally ensure everyone who ever made you feel less than the beautiful, wonderful soul you are because you’re trans will go straight to Hell when they die. He’s smiling when he says it but the coldness in his eyes reminds you that he and Lucifer really are related.
  * Bonus: he may be an agent of God, but he is definitely no innocent virgin. You don’t make it home for dinner that night.



Diavolo

  * He’s the demon prince, so of course he’s going to make sure your first date shows you the best that the Devildom has to offer!
  * First stop is dinner at Ristorante Six. He’s a perfect gentleman, holding the door open for you and pulling out your chair before he sits down himself. Of course he’s paying, and he insists you order whatever you’d like. If you’re not sure what some of the more obscure Devildom dishes are, he’s happy to explain them to you and compliments your excellent taste no matter what you order.
  * He keeps you roaring with laughter throughout the entire meal. The conversation flows so easily that you don’t even notice how late it’s gotten when a server comes to tell you the restaurant is closing for the night.
  * Diavolo suggests you take a walk in his favorite park before he brings you home. He’s so easy to talk to, even though you’re getting tired you don’t want the date to end just yet.
  * Eventually, though, he notices you’re growing sleepy, so he insists on walking you back to the House of Lamentation. He pauses at the entry gate, stalling so the date lasts just a few minutes more.
  * The conversation finally falls into a lull that neither of you are willing to break. Diavolo’s looking at you like he’s torn between being a gentleman and just giving into his desires. 
  * He starts to lean toward you, carefully, like he’s waiting for your permission.
  * You want to kiss him so, _so_ badly, but something is stopping you. You were nervous to tell him you’re trans because he was just so wonderful and you didn’t want to scare him away, but something about him makes you feel you can trust him. You want him to know before things go any further between you.
  * After you tell him, he sheepishly informs you that he already knew. All of your personal information was in your file when he was reviewing candidates for the exchange program.
  * At first you’re mortified, but he quickly assures you he has zero problem with it. He didn’t want to say anything because it wasn’t his place to bring it up, so he was waiting for you to feel comfortable enough to tell him.
  * After that, you’re completely certain that you can trust Diavolo to support you no matter what. 
  * You’re ready for that kiss now.



Barbatos

  * It takes some convincing to get him to take a break from Diavolo long enough for a real date with just the two of you. His work ethic and loyalty are two of the traits you admire most about him, but you’re relieved to get some one-on-one time.
  * You invite him to a new tea house that just opened downtown. You figured he would appreciate the opportunity to enjoy tea he didn’t have to make himself.
  * Any fear you might have had that you would run out of things to talk about disappears as soon as you arrive. Barbatos seems much more relaxed and his smile is genuine. He even laughs at your awful tea puns, bless him.
  * It’s a rare opportunity to learn more about him, and you don’t waste it. He lets his guard down a bit and tells you more personal details about his life and how he came into Diavolo’s service.
  * Then he starts to ask more about you.
  * Instantly you clam up. You don’t much like talking about your life in the human world, but Barbatos was so open about sharing with you. It would only be fair to do the same…
  * Sensing your hesitation, he assures you that you do not have to tell him anything personal if you don’t want to. But the way he’s been treating you all afternoon, showing you such respect and kindness- you want to trust him.
  * So you tell him about coming out as trans and how your family rejected you. Before you were summoned to the Devildom, you weren’t sure how much longer you could have survived up there. In many ways, the exchange program saved you.
  * Barbatos is quiet for a long moment, but it isn’t uncomfortable. Finally, he puts a hand over yours- the first physical contact he’s shown since you met- and assures you that you didn’t deserve that treatment, and he will do anything he can to help you understand how much he appreciates and supports you- _all_ of you.
  * The wounds from your family’s rejection are still tender, but with Barbatos’ support, the pain feels a little more tolerable.



**Notes for the Chapter:**

> See the next chapter for Asmo's part! Thank you for reading :)


	3. Asmo's first date with Trans!MC*

**Summary for the Chapter:**

> Prompt: Trans!MC’s first date with the boys (cont’d)  
> Characters: Asmo  
> Rating: Romantic/NSFW  
> Content: high fashion, Asmo being extra, alcohol consumption, tipsy makeouts (with clear consent), french kissing, discussion of transphobia and shitty families, rough blowjob, oral, lingerie, face sitting

**Notes for the Chapter:**

> This is a continuation of the previous chapter! I saved Asmo for last because he's my fave and then it ended up being disgustingly long so I thought it would work better as its own chapter. Enjoy!

  * He’s been asking you out for weeks, but you always said no because you were afraid that if you let him get to know you better, he’d stop wanting to hang out with you. Self esteem issues are a bastard.
  * Finally, after many suggestive texts and romantic gestures, he wears you down and you agree to a date. You’ve lived together for more than a month and he’s still making all this effort to get you to go out with him, so maybe this won’t be a total disaster.
  * Naturally, Asmo goes all out. He wakes you up with breakfast in bed and starts styling your hair while you eat. He scoffs at the clothes in your closet and declares that you’ll need an _extra_ special outfit for this occasion. He drags you to his room and pulls together an ensemble that somehow fits you perfectly and accentuates all your best features.
  * Once he’s deemed your appearance worthy of leaving the house, he whisks you down to the beach to check out the annual sandcastle competition. Some of them are actual castles, the size of small houses, that you can walk through and admire the artistry. After that you stroll along the boardwalk and chat, enjoying the warm weather and each other’s company.
  * When you stop to take a quick rest, he looks out at the demons swimming around in the ocean and suggests the two of you join them. When you remind him you don’t have a bathing suit, he winks and says that maybe the two of you should find a private beach for a little skinnydipping.
  * At the look on your face, he laughs and says he was kidding… mostly. You’re just too cute when you’re flustered.
  * He treats you to ice cream and you eat together on a covered bench near the ocean so you can people watch. You suggest a game you used to play with your friends all the time, where you make up backstories for random people in the crowd. You two have a blast creating the most dramatic stories.
  * When you start to get tired from walking around, Asmo calls a cab to bring you to your next destination: a new art exhibit from some Devildom sculptor you’ve never heard of. You’re surprised by Asmo’s knowledge of art history and his insightful commentary on the pieces. You’re content to follow him around and listen to him talk, occasionally sprinkling in comments about how he’s the _real_ masterpiece here.
  * After the exhibit, he brings you to a chic cafe. It’s a bit early for dinner, but Asmo enigmatically replies that you’ll thank him later.
  * Once you’re satisfied, he sweeps you along to the next stop on the date. He brings you to the mall to pick out a fancy new outfit. When you ask what’s wrong with the clothes he lent you, he looks positively scandalized and responds that nothing less than the finest will do for your next destination.
  * He sweeps through stores like a tornado, gathering stacks of clothes for you to try on. It feels like you’ve gone through hundreds of outfits- which he insists you model for him- before you both agree on a dazzling number that reveals just enough skin to be enticing, but is still appropriate for whatever event you’re going to later.
  * One of the perks of being Asmo is that he always gets a private dressing room in every store. He lounges on a plush couch and watches you try on each outfit. At your insistence, he allows you to change behind a divider, but you can see his eyes roaming your body when you step into his sight.
  * When you find the perfect outfit, he actually starts to salivate.
  * He invites you to join him on the couch, but you know that if you do it will be almost impossible to tear yourself away from him, so you decline with the promise to make it up to him later. He will definitely hold you to that.
  * A sleek white limo greets you when you leave the mall. You change into your new outfit in the back (making Asmo promise to cover his eyes, though you’re sure he tried to sneak a look). You ask why he didn’t get a fancy new outfit, but he just hums mysteriously.
  * The limo pulls up outside of an immaculate modern building. A crowd of fans and paparazzi pushes against the barriers lining the gold carpet which leads from the sidewalk up to the entrance doors. Asmo takes your hand and before you can ask any questions, drags you out of the limo.
  * Immediately the crowd erupts in cheers. Asmo basks in the attention, waving and blowing kisses to his fans. You hold onto him and try not to trip on your own feet as he leads you into the building.
  * Bodyguards in neat suits appear and whisk your date down a side hall. You call after him but he assures you that everything is fine. 
  * Another bodyguard escorts you down another hall and into a huge room packed with demons in expensive-looking formalwear. In the center of the room is a stage shaped like a big T. A huge banner reads “490th Annual Devildom Fashion Exposition.”
  * You’re led to a seat marked off with a gold ribbon and a little sign with your name on it. Moments later, the lights change color and pounding techno music fills the room. Gorgeous models in designer clothes strut onto the runway.
  * The lights dissolve into brilliant shades of pink, delicate bubbles drift over the crowd, and then Asmo steps onto the stage, decked out in the most captivating ensemble you’ve ever seen. Every eye in the room is glued to him as he saunters down the runway. The way he moves is like lust incarnate, sex on legs, drawing every onlooker into the sway of his hips and the graceful arch of his calves, the curves of his chest and sharp cut of his collarbones. You can’t help feeling a little bit of pride. _That’s my date!_
  * He locks eyes with you, and for that moment you forget that you’re surrounded by demons. He leans down and extends a hand to you. You don’t hesitate to accept it, and then he pulls you up onto the stage and sweeps you into his arms.
  * The crowd goes nuts. You’re overwhelmed by the noise, the thrill of the moment, and all you can do is laugh as you cling to Asmo. He carries you bridal-style up the runway and blows one last kiss to the crowd before taking you backstage.
  * He sets you down and then immediately has to hug you to him because your legs are shaking so hard from adrenaline you can’t stand up. He brings you to his dressing room and makes sure you’re comfortable and have everything you need before he goes back for his next turn on the runway. You’ve had more than enough of high fashion and are perfectly content to wait there for him.
  * After the show is finally finished, he returns to the dressing room and collapses on top of you on the futon. Even covered in sweat and panting like he just ran a marathon, he really is one of the most beautiful creatures in all the realms.
  * You convince him to sit up and drink some water. While he cools down, you take off his high heels and give him a foot rub that has him melting into the cushions.
  * “I was going to take you to the afterparty, but now I’m more tempted to just keep you here all to myself.”
  * Even exhausted, though, he can never resist a good party. Once he’s rested up and changed into comfortable clothes, he calls a cab to bring you to The Fall. The line to get in stretches two blocks and everyone pushes over each other to try and get a glimpse of Asmo climbing out of the cab.
  * You get quite a few jealous stares as he puts an arm around your waist and strolls right into the club.
  * The place is stuffed with models, agents, designers, and various other demons that you’ve only seen on the pages of fashion magazines. All of them greet Asmo like a close friend and eye his newest arm candy with interest. _It’s just like him to bring a_ human _to a party. He’s always trying to show us up…_
  * You start to feel nervous at some of the more malevolent glares being thrown your way, and are abruptly reminded of how weak and powerless you really are in this crowd full of demons.
  * Asmo notices your nervousness and assures you that no one would dare hurt you as long as you’re at his side. If anyone tried, well…
  * His fanged smile makes you shudder with a primeval fear.
  * He doesn’t stop touching you all evening. If his arm isn’t wrapped around your waist or shoulders, he twines his fingers with yours or leans his head against yours. When you dance, he makes sure as much surface area of his body as possible is pressed to yours, teetering along the line of indecency.
  * The touches only get more intimate as the night goes on, until he’s literally straddling your lap in a corner booth as he sips on a neon pink cocktail. He offers you a sip and you hesitantly accept.
  * Instead of handing you the glass, he presses his lips to yours in a sudden kiss. You’re so surprised that you don’t resist when he pushes his tongue between your lips and lets you taste the lingering flavors of his cocktail.



He reaches up to cradle your cheek in one hand, gently tilting your head so that he can deepen the kiss. He moans when you part your lips to allow him greater access. You tighten your grip on his waist like you’re afraid you might float away on a cloud of bliss.

He breaks the kiss with a gasp and leans back to stare at you. His cheeks are flushed a delicate pink, honey-peach eyes wide with awe. You imagine you must look a similar sight with the way he’s looking at you, like you’re something precious that just fell from the sky and knocked him in the head.

He licks his lips. “So? How is it?” he murmurs.

You smirk up at him. “Hmm, I don’t know,” you hum, “I think I need another taste just to be sure.”

His lips break into a glowing smile before they meet yours once more. He tastes fruity and sweet, like strawberries and cream, with an undercurrent of cherry liqueur that makes your head spin. His skin is unbearably soft and his perfume caresses your senses, a light floral scent like crushed violets that’s both dizzying and overwhelming. It makes you want to get as close to him as you can, burrow beneath the dazzling outer layer and into the soft vulnerabilities beneath, make your home among the things that no one else knows about him.

You snag his bottom lip between your teeth and bite hard enough to make him squeal in delight. He shifts in your lap and your heart jumps when you feel the unmistakable press of his erection against your thigh.

Asmo pulls back, panting, and leans down to your ear to gasp, “If you keep that up, I may just devour you right here.”

The thought is tempting… but your common sense wins out, and you gently push him off of your lap. “Then I suppose we’d better hurry home,” you reply.

He grabs your hand and drags you through the crowded club, not even bothering to acknowledge the partygoers who call out to him as he passes. Before you can fully process what’s happening, he’s hailed a cab and handed the driver an extra hundred grimm to take the shortest route back to the house.

He spends the ride pressed against you, fingers clasped around your own, though he doesn’t move to touch any other part of you. A few times he fidgets uncomfortably and tugs the hem of his jacket down over his lap, which makes you smirk.

When you’ve finally,  _ finally _ arrived home and made it upstairs without encountering any of his brothers- for which you quietly thank the fates- Asmo tugs you into his room and quietly shuts and locks the door.

With the harsh  _ click _ of the lock, a wave of clarity crashes over you. Your confidence from earlier is replaced with a sudden anxiety; your legs feel weak and your heart begins to race with nerves rather than excitement.

Asmo places a comforting hand on your shoulder. “Darling,” he says, “are you feeling well?”

You nod numbly, but it doesn’t fool him. He leads you over to the bed and guides you to sit down next to him. He whispers something in a language that makes your bones ache, but then there’s a rush of calm, like finally removing a clothing tag that was bothering you.

“It’s a sober spell,” Asmo answers your unspoken question. “Not that either of us was shitfaced drunk or anything, but I find these things tend to be much more comfortable with a clear head.”

You turn your face to press against his shoulder in a silent thanks. He holds you against his side with one hand and reaches up to stroke your hair. The action is so unexpectedly sweet after everything leading up to this moment that you find yourself, to your own mortification, beginning to tear up.

“What’s wrong?” Asmo pulls his hand away, a note of panic in his voice. “Is it me? Did I hurt you? Did I go overboard again?” He drags a frustrated hand through his hair. “I’m so sorry, dear, I just wanted to impress you. I didn’t think- I’m so sor-”

“It’s not your fault,” you say quickly. He’d started to move away from you on the bed, but you put a hand on his thigh to anchor him to your side. He swallows hard and his eyes dart from your hand back to your face.

“What is it? Tell me and I’ll make it better,” he whispers.

You sigh and fix your eyes on the floor. You’ve never told this to anyone else, only reliving the memories on your worst nights when you feel like having a really good cry. There’s already a headache forming just behind your eyes as your tear ducts anticipate what will happen next.

“Back home, in the human world,” you begin, voice hoarse from pushing through the lump forming in your throat, “I didn’t have the most… accepting family. They were very conservative and traditional, and- well, I’m sure you know how cruel humans can be when their beliefs are challenged.”

You glance sideways at Asmo. He’s watching you intently, giving you every sign of his full attention, so you carefully resume the story. “It took me a really long time to realize… I mean, I never liked the clothes or toys that were forced on me growing up, and I hated the idea of becoming just like my parents. Settling for a loveless marriage with two children and a picket fence because that’s what I was supposed to want.”

The tears are starting to push out, but you force them back. “When I was in high school I started hanging out at the library more often so I could secretly go on the internet without my parents knowing. And as kids do, I asked questions, and I found out there was a word for what I was, and it felt… I don’t know. Natural, I guess?”

You look up at Asmo, but his face is blurry and skewed. You realize that the tears have finally climbed out and welled in your eyes. You blink and feel them run hot over your cheeks. Asmo’s sympathetic expression comes into focus.

“I was sixteen when I came out to my parents as trans. You can imagine how that went.” You sniffle and hastily wipe your eyes with the backs of your hands. You can’t stand his pity so you focus on the floor again. “Anyway, they kicked me out and I couch surfed for a while until I made it to the city where there was a shelter for LGBT+ youth. They took me in, no questions asked. Helped me get back on my feet and figure everything out.”

You take a deep, shuddering breath and look back up at Asmo with what is likely an unconvincing smile. “And then I ended up here.”

He tilts his head, regarding you with curiosity, and you realize that his own eyes are glistening with unshed tears. He reaches for your hand and you let him take it gently in his own.

“Does anyone else know?” he asks.

“Diavolo and Lucifer probably know since they picked me for the program. But you’re the first person I’ve told the whole story to.”

He blinks slowly and the tears carve twin paths through his makeup. “Thank you for trusting me,” he whispers earnestly.

You shrug one shoulder, suddenly crushingly self-conscious under the intensity of his stare. “Yeah, well. I kinda really like you, so. I thought you should know.”

A brilliant grin breaks out through his tears. “You have no idea how happy it makes me to hear that, love.”

He abruptly straightens up and shakes himself as if warding away a nightmare. He leans over and opens his bedside table- still clutching your hand in his other one- and pulls a packet of tissues from the drawer. He offers them to you, which you take gratefully. The frail paper feels unexpectedly soft against your skin.

“They’re infused with shea butter so your skin doesn’t get ruined,” Asmo explains.

“Only the best for the most gorgeous demon in the realm,” you tease. He smiles and preens at the compliment.

When you’ve both cleaned up, Asmo tosses the tissues in his wastebasket and then scooches up on the bed so he can lie back against his mountain of pillows. He uses his grip on your entwined fingers to tug you up next to him. You giggle at his wide, begging eyes, but assent to his request and lie down beside him.

He brings your hands up to his face and kisses your knuckles reverently. You relax back onto the pillows and watch him through half-lidded eyes. His lips feel heavenly on your skin. After the busy day you’ve had, it feels so nice to just lie down and enjoy his company. 

He pokes your cheek and gives a disgruntled frown. “You’re not going to sleep on me yet, are you? It’s not even midnight,” he pouts.

You roll your eyes and poke him back. “I can’t help it. You wore me out today.”

“Hm, I suppose that’s true.” He wraps his free arm around your waist and pecks your nose playfully. “I guess you’ve earned a rest, then. So long as you agree to sleep next to me~”

Your shirt has ridden up and a burst of heat explodes where his fingers brush over your bare waist. You rake your eyes over Asmo’s relaxed expression, the lounge clothes covering too much of his body- making you hungry to see more of him. Your heart stutters at the thought.

“Actually,” you muse, “I don’t know if I’m quite ready to go to sleep just yet.”

He smirks. “Oh? Then what would you rather do instead?” 

“Hmmmm…” You disentangle your hand from his and stroke it through his wavy hair. “I have a few ideas. I don’t know if you’d like them, though…”

“Tell me,” he demands.

You tsk-tsk. “Ask me nicely and I might consider it.”

Asmo whines and shifts closer to you, tightening his grip around your waist so you’re anchored together at the hips. His sweet breath ghosts over your cheek as he leans up to your ear and whispers a plaintive, “ _ Please _ .”

Something snaps in you. You hook your leg around Asmo’s waist and roll so that you’re kneeling over him. He doesn’t resist when you grab his wrists and press them into the pillows on either side of his head. He smiles dreamily up at you and bites his lip in anticipation.

“Hey. Consent check,” you say. “Is this what you want?”

“Darling, do you really need me to answer that?” he sighs. “ _ Yes _ , I would very much like you to rail me into oblivion, if you would be so kind.” His expression sobers for a moment. “Are you sure you’re okay? We don’t have to if you don’t-”

You silence him with a kiss. “I’m definitely sure.”

He captures your lips in another kiss. You adore the way his chest arches as he struggles to reach you while you have his hands restrained. You squeeze his skinny wrists, just to feel how weak it makes him, and he lets out a shaky moan. He writhes against you, silently begging for more of your touch.

Normally you would want to draw it out and make him beg, but just this once, you feel like indulging him. You drag your hands along his arms, scratching your nails enough to sting but not to mark his flawless skin. When you reach his shoulders, you let go to tangle your fingers in his gorgeous locks and give a gentle tug.

The wanton gasp that rips itself from his throat makes your skin buzz with pleasure. You pull on his hair again and pair it with a sharp nip to his lower lip. The action makes him cry out in arousal and squirm against you.

“That f-feels so good,” he moans. “Please, can I have some more? You don’t need to b-be gentle with me.”

Your throat goes tight. You’re afraid that your voice will betray how much of an effect he’s having on you, so you respond by yanking his head back and latching onto his pulse point. You suck and nibble at the supple skin while he writhes against you, rolling his hips against your own in a desperate bid for friction. 

“Oh  _ fuck _ ,” he whines. “That’s so good, so- oh, god.” He swallows back a groan. “I need more of your touch, please, darling. Please touch me.”

“But I  _ am _ touching you, Asmo,” you tease.

“You know what I mean!” he huffs. He tries to grind his hips against you but you hold yourself just out of reach. He keens in frustration.

“Why are you being so cruel?” he fusses.

You disentangle your hands from his hair and sit up, holding yourself above him just too far for him to reach. He obediently keeps his hands on either side of his head, though his fingers twitch like they yearn to reach for you. His skin is flushed and his throat is marred by a purpling hickey. His slender chest heaves with desperation, eyes glimmering with tears of need. He’s absolute perfection.

You slide your hands beneath his blouse and make your way up. He shudders at the sensation of your skin sliding over his. You tease over his nipples, gently stimulating the sensitive flesh until he’s squirming. Then you pinch the skin between your fingers and  _ twist _ , and Asmo’s entire body convulses in arousal as a shriek rends itself from his lungs.

He collapses back against the pillows and moans softly. “Oh, god. Thank you…”

“Good job using your manners,” you tease.

He sucks in a sharp breath and moans again. You raise a curious eyebrow. “Does someone have a praise kink…?”

“M-maybe…” he whispers.

You tweak his nipples again and he yelps in surprise and pleasure. He stares at you through half-lidded eyes, lips parted around quick, needy breaths. You smirk at his debauched state.

You tug at the hem of his shirt and he quickly shucks it over his head. The sight of his lean torso, so much soft, kissable skin, makes you dizzy.

“You’re so pretty like this, Asmo,” you murmur. “Of course, you’re pretty all the time. But I think this side of you might be my new favorite.”

He bites his finger and gives you a pleading look. “Please touch me some more? In other p-places,” he whispers.

You lean down to press a lingering kiss below his jaw. “Thank you for asking politely.”

You shuffle farther down the bed and tug at his pants zipper. He whimpers and pushes his hips up into your hand, and you immediately let go of him and deliver a sharp smack to his inner thigh. The pain makes him gasp and writhe.

“Patience, darling,” you say in a honey-sweet voice. He nods meekly and settles back to allow you to remove his pants at your own agonizingly slow pace.

As soon as you get them off his hips, your mouth starts to actually  _ water _ at the sight of the lingerie he was hiding beneath. It’s made of sheer black lace, with a strip of silk conveniently located to hide his cock from you and leather straps that hug his thighs.

“What’s this?” you coo as you tug his pants off the rest of the way. “Did you put these on especially for me, baby?”

“Yes,” he whimpers. “D-do you like them?”

You lean down and press feather-light kisses along his inner thighs, interspersed with gentle love bites until his skin is mottled purple. Then you press your tongue to the fabric covering the base of his cock, lock your eyes onto his own desperate gaze, and lick a long strip along his length.

His back arches and he twists his fingers into the fabric of the pillows. “How does it feel s-so good? You’ve barely touched me and I already feel like my skin is on fire,” he whines.

“Mm, maybe I’m just that good.” You smirk up at him as you press a line of kisses along his cock.

“Ohhhh, shit. Please can you take off my panties? I wanna know how your mouth feels,” he begs.

“Of course, darling.” You hook your fingers under the leather straps and ease the skimpy fabric down his legs. “See how nice I am when you use your manners?”

“Thank you, thank you. Oh~”

His voice dissolves into a pleased groan as you wrap your lips around the tip of his cock. You’re just applying the smallest amount of teasing with your tongue, but he’s mewling and squirming like it’s the greatest pleasure he’s ever felt. He does his best to keep his hips still, his hands roaming over his chest and tugging at his hair, desperate to expel the sensations of his arousal before he combusts.

You wrap a hand around the base of his cock and use your other to steady yourself as you take in a bit more. You move slowly, bobbing your head down just a little bit more at a time, and all through it Asmo is gasping and murmuring mindless praise. It’s difficult to focus between the beautiful noises he’s making and controlling your breathing so you don’t gag on him. Even though you haven’t even touched yourself yet, your arousal is building quickly just from going down on him.

“Oh, just like that- yes- please don’t stop, darling, I’m so close,” he whines.

You pull back a bit and focus your efforts on the head while your hand continues to stroke him. Asmo shrieks and bucks into your mouth, no longer caring about manners as he gets closer to his peak. You want to reprimand him, but then you glance up- you see his face contorted in bliss, eyes screwed shut and plush lips parted around low, warbling moans- and you want nothing more than to make him come.

You can feel tremors rolling through his body as he ascends toward his climax. Suddenly there’s a pressure on the back of your head and you nearly choke as you’re made to take far more of his cock than you were prepared for. You struggle to breathe through your nose and allow him to take his pleasure.

He can no longer form words, just senseless fragments of praise and pleas. His grip tightens in your hair, his hips tense, and you have just a moment to prepare yourself before he spills into your throat with a broken cry.

He lets go of your hair and collapses, boneless, against the pillows. You roll onto your side and stifle a coughing fit as your breath returns. When you feel well enough to sit up, you see Asmo looking meekly at you.

“I’m sorry,” he sniffs. “I didn’t mean to be so rough with you. Are you hurt?”

You do a mental checklist. Other than feeling a little hoarse, you’re just fine. More than that, you’re still insanely aroused.

You crawl up the bed to sit next to Asmo. “Is it weird that I’m still super turned on?” you ask with a shy smile.

His lips form a mischievous smirk. “It’s only natural, darling. I  _ am _ the Avatar of Lust, you know.” He slides a hand beneath your shirt and brushes his fingers over your stomach. “How about I return the favor, hm?”

With Asmo’s help, you tear the rest of your clothes off and carefully straddle his face.

You swallow down your nerves. “You sure about this? I don’t want-  _ oh! _ ”

The rest of your sentence is swallowed in a surprised moan as he wraps his arms around your thighs and tugs you down to meet his lips. Pleasure explodes between your thighs and you have to grab onto the headboard to keep yourself upright. Your legs tremble with the intensity of the sensation.

“Fuck, Asmo. You are way too good at this,” you groan. He hums against you and then does something with his tongue that makes your vision white out for a few seconds.

It’s weirdly intimate being over him like this, but it also makes you feel powerful. And with the way he’s being so submissive for you, so eager to taste you- it’s doing  _ things _ to your body. You feel like someone attached jumper cables directly to your heart. It’s hammering against your ribcage and flooding your skin with dizzying heat, making your eyes roll up into your head.

You gasp as he does something to hike up the pleasure another level. Tears are forming from the stimulation. The bed frame creaks from the force with which you’re grasping it.

“I’m g-gonna come soon,” you gasp. “Asmo, please… p-please don’t stop!”

He lets out a muffled moan and redoubles his efforts to bring you pleasure. Something ferocious seizes in your gut and you snatch a fistful of his hair to anchor yourself. 

Your orgasm unfurls like a volcanic explosion, lungs burning, tears falling, skin hot, aftershocks rushing through you and leaving you quaking. You don’t recognize the unholy sound that rips out of your lungs. Your fingers tremble as you hold onto Asmo’s hair and roll your hips, riding out wave after wave of delicious pleasure until it finally wanes to a heavenly buzz.

You throw yourself onto the pillows beside him, feeling like you just stepped on a live electrical wire. Beside you, Asmo is melting into the bed, licking his lips to gather every drop of your arousal. He turns to you, panting heavily but smiling like there is nothing wrong in the world.

“So,” he says, “on a scale of one to ten, how was that for a first date?”

You bark out a laugh. “Hmm… I guess I’ve had worse.” At his scandalized look, you roll over to wrap him in a lazy half-hug. “Kidding. Best date I’ve ever had, no question.”

“That’s what I thought,” he says smugly. You giggle and press a quick kiss to his forehead.

“Although,” you add, “No one ever said it has to end just yet.”

He perks up at that. “Oh? What did you have in mind?”

You roll him onto his back and lean up on one forearm. Your other hand snakes over his stomach and brushes against his still-hard cock.

“I can’t believe you got  _ this _ turned on just from giving me head,” you giggle.

“Ahh, don’t make fun of me,” he whines. “It’s your fault for being so cute! You should take responsibility.”

“Mm, and how should I do that?”

He gazes up at you with pure adoration shining in his honey-peach irises. “Fuck me,” he whispers.

A wave of arousal washes over you and the tingling aftershocks of your orgasm turn into a pleasant buzz. You lean down to kiss him and he meets you with equal passion.

You pull back to take one more good look at him. You want to always remember the way he looks when he’s horny- lips swollen with kisses, neck littered with hickies, eyes wide and desperate as he lays himself out for you like a fucking banquet. He’s absolutely gorgeous, there’s no doubt, but there’s something else. There’s an undercurrent of warmth that overwhelms you with the urge to praise and treasure him.

“Hey, Asmo?” you whisper.

“Yes?” he hums.

“Thank you for listening, and- you know, being there for me.” You glance away as a sudden embarrassment washes over you. “I’m not great at being vulnerable with other people, and it’s been a long time since I felt like I could trust someone like you. So… thanks.”

He caresses your cheek with a tender smile. “I know it can be hard to open up, but I hope you know how much I care for you. You didn’t choose your biological family, but I hope my brothers and I- well, mostly me- can be like your family.”

He leans up and presses the sweetest kiss you’ve ever felt against your lips. “There is nothing I wouldn’t do to make you happy. Please remember that.”

Your head is spinning. Your chest suddenly feels much lighter… is this what it feels like to have someone you know you can trust? It’s strange, but not unwelcome.

You smile and nuzzle his cheek. “Thank you, Asmo,” you whisper.

“You’re welcome, darling.” He slides his hands over your bare backside and gives it a cheeky squeeze. “Now how about I show you exactly how much I care for you?”


End file.
